p-Toluenesulfonic acid → HCID 66819831, compound

HRID 880828Notes

Reaction equation

HRID 880828 reaction equation
[F:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6]([O:19][CH2:20][CH2:21][O:22]C3CCCCO3)=[C:7]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)[NH:8][C:9]2=[O:12])=[CH:4][CH:3]=1.C1(C)C=CC(S(O)(=O)=O)=CC=1>CO>[F:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6]([O:19][CH2:20][CH2:21][OH:22])=[C:7]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)[NH:8][C:9]2=[O:12])=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 6101p-Toluenesulfonic acidHCID 66819671HCID 66819671, compound

Product 1

HCID 66819831HCID 66819831, compoundYield 95%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
55 °C

Procedure

To a solution of 590 mg (1.54 mmol) of 7-fluoro-3-phenyl-4-[2-(tetrahydro-2H-pyran-2-yloxy)ethoxy]isoquinolin-1(2H)-one in methanol (12 mL), 88 mg of p-toluenesulphonic acid (0.46 mmol) were added and the resulting mixture was heated at 55° C. for 2 hours. The solvent was removed under reduced pressure and the residue was diluted with dichloromethane and washed twice with aqueous sodium hydrogencarbonate saturated solution. The combined organic layer were dried over sodium sulphate and concentrated under reduced pressure to afford 438 mg of the title compound (95%).

Workup

  1. customThe solvent was removed under reduced pressure
  2. additionthe residue was diluted with dichloromethane
  3. washwashed twice with aqueous sodium hydrogencarbonate saturated solution
  4. dry with materialThe combined organic layer were dried over sodium sulphate
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-ac7226b3b76142e385f36bc32fd46050
Source dataset
uspto-grants-2015_03
Patent number
US08993594B2

Reaction notes

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